Potassium Carbonate → 2,4-Diphenylaniline

HRID 75073

Reaktionsgleichung

Br[C:2]1[CH:8]=[C:7](Br)[CH:6]=[CH:5][C:3]=1[NH2:4].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:10]1([C:2]2[CH:8]=[C:7]([C:2]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:3]=3)[CH:6]=[CH:5][C:3]=2[NH2:4])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

2,4-dibromoaniline (10 mmol), benzeneboronic acid (24 mmol), tetrakis(triphenylphosphine)palladium(0) (1 mmol) and potassium carbonate (12 g) are put in a two-neck round-bottom flask and dissolved in toluene (30 mL) and H2O (10 mL). Subsequently, the resulting solution is stirred in a bath under a temperature of about 100° C. for 24 hours. After completion of the reaction, toluene is removed. The reaction mixture is extracted with dichloromethane and water, and then being distilled under reduced pressure. The resulting residence is filtered by silica gel column and distilled under reduced pressure again. Next, by re-crystallizing and filtering with dichloromethane and petroleum ether, 2,4-diphenylaniline (2.0 g) is yielded.

Aufarbeitung

customis removed
extractionThe reaction mixture is extracted with dichloromethane and water
distillationbeing distilled under reduced pressure
filtrationThe resulting residence is filtered by silica gel column
distillationdistilled under reduced pressure again
customNext, by re-crystallizing
filtrationfiltering with dichloromethane and petroleum ether

Quellen und Nachweise

ORD-Eintrag: ord-8b5da7c99c7443219ca237e017646c49
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08835020B2

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